cis-1,2-dibromo-1,2-dimethylcyclopropane | 85739-31-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: cis-1,2-dibromo-1,2-dimethylcyclopropane
• 英文别名: (1S,2R)-1,2-dibromo-1,2-dimethylcyclopropane
• CAS: 85739-31-7
• 化学式: C₅H₈Br₂
• 分子量: 227.927
• InChiKey: RCQQXMINMMTLKH-SYDPRGILSA-N

物化性质

• 沸点：
  156.3±15.0 °C(Predicted)
• 密度：
  1.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,3-二苯基异苯并呋喃 、 cis-1,2-dibromo-1,2-dimethylcyclopropane 在 甲醇 、 叔丁基锂 作用下， 生成 9,11-dimethyl-1,8-diphenyl-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-triene
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.

  DOI：

  10.1021/ja00021a024
• 作为产物：
  描述：

  1,2-二甲基环丙烷-1,2-二羧酸 在 溴 、 magnesium sulfate 、 mercury(II) oxide 作用下， 生成 cis-1,2-dibromo-1,2-dimethylcyclopropane 、 trans-1,2-dibromo-1,2-dimethylcyclopropane
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.

  DOI：

  10.1021/ja00021a024